Benzoic acid (3R,5R)-2-oxo-5-((Z)-propenyl)-tetrahydro-furan-3-yl ester

Base Information

• Chemical Name: Benzoic acid (3R,5R)-2-oxo-5-((Z)-propenyl)-tetrahydro-furan-3-yl ester
• CAS No.: 77523-33-2
• Molecular Formula: C₁₄H₁₄O₄
• Molecular Weight: 246.263
• Mol file: 77523-33-2.mol

Synonyms:Benzoic acid (3R,5R)-2-oxo-5-((Z)-propenyl)-tetrahydro-furan-3-yl ester

Chemical Property of Benzoic acid (3R,5R)-2-oxo-5-((Z)-propenyl)-tetrahydro-furan-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (3R,5R)-2-oxo-5-((Z)-propenyl)-tetrahydro-furan-3-yl ester

There total 6 articles about Benzoic acid (3R,5R)-2-oxo-5-((Z)-propenyl)-tetrahydro-furan-3-yl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

benzoyl chloride (98-88-4) + (3R,5R)-3-Hydroxy-5-((Z)-propenyl)-dihydro-furan-2-one (77523-41-2) → Benzoic acid (3R,5R)-2-oxo-5-((Z)-propenyl)-tetrahydro-furan-3-yl ester (77523-33-2)

Guidance literature:

With pyridine; In dichloromethane;

DOI:10.1021/ja00397a059

Reference yield:

(3aR,5R,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole-5-carbaldehyde (14260-67-4) → Benzoic acid (3R,5R)-2-oxo-5-((Z)-propenyl)-tetrahydro-furan-3-yl ester (77523-33-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 69 percent / KO-t-Bu / tetrahydrofuran

2: 1.) PTSA, 2.) Ag₂CO₃/celite / 1.) CH₃CN, H₂O, 2.) benzene

3: 95 percent / pyridine / CH₂Cl₂

With pyridine; Celite; potassium tert-butylate; toluene-4-sulfonic acid; silver carbonate; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja00397a059

Reference yield:

D-glucose (50-99-7) → Benzoic acid (3R,5R)-2-oxo-5-((Z)-propenyl)-tetrahydro-furan-3-yl ester (77523-33-2)

Guidance literature:

Multi-step reaction with 6 steps

1: ZnCl₂, H₃PO₄ / 72 h / Ambient temperature

2: 82 percent / pyridine

4: 69 percent / KO-t-Bu / tetrahydrofuran

5: 1.) PTSA, 2.) Ag₂CO₃/celite / 1.) CH₃CN, H₂O, 2.) benzene

6: 95 percent / pyridine / CH₂Cl₂

With pyridine; phosphoric acid; Celite; potassium tert-butylate; toluene-4-sulfonic acid; silver carbonate; zinc(II) chloride; In tetrahydrofuran; pyridine; dichloromethane;

DOI:10.1021/ja00397a059

upstream raw materials:

benzoyl chloride

(3R,5R)-3-Hydroxy-5-((Z)-propenyl)-dihydro-furan-2-one

(3aR,5R,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole-5-carbaldehyde

D-glucose

Downstream raw materials:

2-[(1R,5R)-5-Benzoyloxy-1-methyl-6-(toluene-4-sulfonyloxy)-hexyl]-malonic acid dimethyl ester

(E)-(3R,7R)-7-Benzoyloxy-2-methoxycarbonyl-3-methyl-oct-4-enedioic acid 1-methyl ester